(1) Field of the Invention
This invention relates to novel 3(2H)-pyridazinone derivatives; preparation thereof; insecticidal, acaridical, nematicidal, fungicidal compositions for agricultural and horticultural uses; and expellent compositions for ticks parasitic on animals; said compositions containin said derivatives as an active ingredient.
(2) Description of the Prior Art
Hitherto, there have been reported various 3(2H)-pyridazinone derivatives which have thioether bonding as in the compounds of the present invention. Among them, there have been known the compounds listed in Table 1 below and the physiological activities thereof.
The physiological activities of all the compounds listed in Table 1 are restricted to fungicidal, central nerve depressing- and/or herbicidal actions. It has not been reported at all that these compounds exhibit excellent insecticidal, acaricidal, nematicidal activities which are found in the compounds of the present invention. The compounds according to the present invention have excellent insecticidal, acaricidal and nematicidal activities in addition to fungicidal action. These activities are attributed to the specific structures of the compounds of the present invention. Namely, the compounds of the invention are unique in that they have a straight or branched C.sub.2 to C.sub.6 alkyl group on the 2-position of the pyridazinone ring and also a substituted benzylthio group on the 5-position of said ring. The prior art literature has disclosed neither the compounds of the invention specifically nor physiological activities such as insecticidal, acaricidal, nematicidal activities of the compounds.
TABLE 1 __________________________________________________________________________ Japanese Patent Publication No. Compound Physiological activity (Publication Date) __________________________________________________________________________ ##STR2## fungicidal action central nerve- depressing 09344/67 (5/11/67) 08860/69 (4/24/69) R: alkyl, benzyl or 4-chlorobenzyl ##STR3## pressor action 11902/68 (5/20/68) 11903/68 (5/20/68) 11904/68 (5/20/68) 08857/69 (4/24/69) 08859/69 (4/24/69) 12421/69 (6/5/69) R: hydrogen or a halogen X: a halogen or thiol ##STR4## pressor action central nerve- depressing action antifungal action 11905/68 (5/20/68) 11908/68 (5/20/68) R: phenyl, furyl or thienyl R.sup.1 : a lower alkyl ##STR5## antifungal action 08860/69 (4/24/69) 08861/69 (4/24/69) R: a halogen or a lower alkylthio ##STR6## pressor action antifungal action anti-acetyl choline action 01302/67 (1/23/67) 11904/68 (5/20/68) 11906/68 (5/20/68) 11907/68 (5/20/68) 11909/68 (5/20/68) 08858/69 (4/24/68) R: phenyl, chlorine-substituted phenyl, pyridyl, furyl or thienyl ##STR7## antifungal action 02459/66 (2/17/66) 02788/66 (2/21/66) X: O or S ##STR8## fungicidal action Chemical Abstracts 93, 114552g R: hydrogen, methyl, ethyl or benzyl ##STR9## fungicidal action Chemical Abstracts 91, 20533h and 74637p ##STR10## R: hydrogen, an alkyl, phenyl or a halophenyl ##STR11## herbicidal action Japanese Patent Publication No. No. 03798/65 R: hydrogen or phenyl R.sup.2 : an alkyl, phenyl, or CH.sub.2 COOH __________________________________________________________________________
All the compounds represented by the general formulae IV through VIII are apparently different from those of the present invention of the formula I given below in that the former compounds have phenyl group at 2-position. On the other hand, the compounds of the general formula IX are also apparently different therefrom in that the 2-position of the former is not substituted. Moreover, the thiol compounds and the salts thereof having the formula X are reported to have fungicidal activity and are different from those of the present invention in that the former have a substituted benzylthio group at 5-position.
The present inventors have conducted intensive research on the preparation of the novel compounds of the formula I given below as well as on activities thereof as an agricultural drug, and have found that the compounds of the formula I are useful for the control of agricultural and horticultural insect pests and acari, for the prevention of blight and for expelling ticks parasitic on animals to accomplish the invention.